Among the lessons David Bowie taught the pop-music world is that the backup can make the frontman, something he proved in the process of subverting the gender specificity in the term “frontman.” Bowie established his reputation as a fiercely original creative force not only by performing his own sonically and sexually venturesome art-pop but also by reinventing other acts behind the scenes. He took a foundering group of folk-rockers called Mott the Hoople and remade them as glam stars with “All the Young Dudes,” the glitter-rock anthem he wrote and produced for the band in 1972. He did much the same thing around the same time for Lou Reed, co-producing the single “Walk on the Wild Side” and the Transformer album that carried Reed out of Velvet Underground culthood and onto the pop charts; and he had nearly as much success with Iggy Pop, recasting the punky singer for the Stooges as an emblem of transcontinental rock intellectualism.

Over the course of his mercurial five-decade career, Bowie enacted many of his celebrated transformations as a performer through strategies of association and collaboration. He was tactical and, as a rule, wise in his selection of creative partners: Brian Eno for Low, Heroes, and Lodger, the triptych of soundscape masterworks of his “Berlin period”; John Lennon for “Fame,” the “plastic soul” single that was his first number-one hit in America; and Bing Crosby for the Christmas-special duet that spun him as a family entertainer. He dallied less fruitfully on a couple of occasions, prancing around with Mick Jagger in the video for their gay-uncle duet of “Dancing in the Street,” and pandering to his lessers on “Falling Down,” a karaoke-night mistake with Scarlett Johansson on her album of Tom Waits covers.

For what he no doubt knew would be his final album, Blackstar, Bowie made one of his most astute choices of collaborators: Donny McCaslin, the leader of a well-respected New York jazz group with a subtly retro art-rock feeling. McCaslin had come recommended by Maria Schneider, the composer and jazz-orchestra conductor, with whom Bowie had recorded a majestic, ethereal single and accompanying video, “Sue (Or in a Season of Crime),” in 2014. Bowie asked Schneider to work with him on additional songs, but she was wrapped up with a new project of her own, the album The Thompson Fields (which has since been nominated for a Grammy and which I named the Best Album of 2015). Schneider suggested that Bowie check out the quartet led by McCaslin, who plays in her orchestra, and Bowie went to hear his band at the tiny 55 Bar on Sheridan Square in Greenwich Village.

McCaslin has been a talked-about presence in New York jazz circles since the early 1990s, when he was playing with Gil Evans as well as in the fusion group Steps Ahead, and beginning his long association with Schneider. Since the late ’90s, McCaslin has released 11 albums as a leader and has been nominated for a Grammy three times—twice for solos on albums by Schneider, once for an improvisation on his own album, Casting for Gravity, released in 2012. The music he makes is ambitious but accessible, unapologetically the work of a person who grew up with rock on the radio. As an improviser, McCaslin is openly, robustly emotive, far more interested in expressing feeling than showing off his considerable technique. His solos sometimes seem almost extra-musical, and they can reach the pitch of a Pentecostal fever.

In the making of Blackstar, Bowie had McCaslin and his quartet—McCaslin on reeds and woodwinds, Jason Lindner on keyboards, Tim Lefebvre on bass, and Mark Guliana on drums and percussion, augmented for the recording by Ben Monder on electric guitar—to play as they do. Bowie brought music he wrote to the band, but freed the musicians to do it in their style. The sound of McCaslin’s group—dense and polyphonic, but propulsive, often biting, became the sound of the album. For Blackstar, McCaslin served much as Bowie had with Lou Reed on Transformer. Bowie enlisted McCaslin to be his Bowie. The result is an album of mature and serious, unpretentiously virtuosic and profoundly emotive music. The lyrics are appealingly cryptic, in the Bowie style, and bleak, dealing implicitly and sometimes explicitly with the themes of loss and decline. It’s grim and beautiful and, with Bowie’s death two days after its release in mind, hard to take in.

McCaslin and his quartet, without Ben Monder, and with Nate Wood on bass, played at the Village Vanguard this past week, and I saw the first set. The band was at its best, with McCaslin playing with such deep feeling that it appeared more than once as if he was on the verge of collapse. At one point, he tried to talk about Bowie, but couldn’t get his name out. He tried a couple of times, and had to turn his head from the microphone. Before the end of the set, he mustered the strength to say a little bit about Bowie before leading the band in a spare, restrained, and wrenching performance of “Warszawa,” a Bowie and Eno collaboration on the Low album. It had been written, in the late 1970s, to evoke the bleakness of Warsaw in the Cold War era, and it conjured a timely sadness this time. “That was David Bowie,” McCaslin said.